Synthesis of α-CF3-substituted carbonyl compounds with relative and absolute stereocontrol using electrophilic CF3-transfer reagents

Václav Matoušek; Antonio Togni; Vincent Bizet; Dominique Cahard

doi:10.1021/ol2023328

Synthesis of α-CF3-substituted carbonyl compounds with relative and absolute stereocontrol using electrophilic CF3-transfer reagents

Org Lett. 2011 Nov 4;13(21):5762-5. doi: 10.1021/ol2023328. Epub 2011 Oct 3.

Authors

Václav Matoušek¹, Antonio Togni, Vincent Bizet, Dominique Cahard

Affiliation

¹ Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, CH-8093 Zürich, Switzerland.

PMID: 21962226
DOI: 10.1021/ol2023328

Abstract

Evans-type chiral lithium imide enolates undergo diastereoselective α-trifluoromethylation with a hypervalent iodine-CF(3) reagent with up to 91% combined isolated yield and 97:3 dr. The resulting isolated diastereopure products can be further transformed into valuable products without racemization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids / chemical synthesis*
Electrons
Fluorocarbons / chemistry*
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

Carboxylic Acids
Fluorocarbons
carbon tetrafluoride